Potassium Carbonate → HCID 59590525, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 2 (3.0 g, 14.6 mmol) in 1,4-dioxane (200 mL) was added a solution of K2CO3 (4.0 g, 29.3 mmol) in water (40 mL). The almost clear solution was placed under nitrogen atmosphere and (1-Ethoxyvinyl)-tributylstannane (5.0 mL, 14.6 mmol) and PdCl2(PPh3)2 (500 mg, 0.731 mmol). The mixture was heated to 100° C. and stirred at 100° C. for 30 min under nitrogen atmosphere. After cooling to room temp. the 1,4-dioxane was removed i. vac. The residue was re-dissolved in DCM (100 mL) and water (50 mL) and transferred to a separating funnel. The aqueous layer was extracted with DCM (30 mL), the combined organic layers were washed with water (50 mL) and sat. brine (30 mL), dried over Na2SO4 and evaporated to dryness i. vac. The residue was purified by flash column chromatography (50 g SiO2 Isolute® pre-wetted with 1CV DCM) eluting with neat DCM collecting 12 mL fractions. Desired product eluted in fractions 10 to 20 with Rf=0.31 (DCM). By-products eluted in fractions 6 to 9 (Rf=0.59 in DCM) and fractions 21-31 ((Rf=0.14 in DCM). Fractions 10 to 20 were combined and evaporated to dryness i. vac. providing 2.28 g (65% yield) 2-chloro-4-(1′-ethoxy-vinyl)-thieno[3,2-d]pyrimidine as yellow powder of 95% purity.

Provenance & Evidence